3D model (Jmol)
|Molar mass||267.41 g·mol−1|
|Main hazards||Highly toxic|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Allopumiliotoxin 267A is a toxin found in the skin of several poison frogs of the family Dendrobates. It is a member of the class of compounds known as allopumiliotoxins. The frogs produce the toxin by modifying the original version, pumiliotoxin 251D. It has been tested on mice and found to be five times more potent than the former version. It has been produced synthetically through a variety of different routes.
- Edwards MW, Daly JW, Myers CW. Alkaloids from a panamanian poison frog, Dendrobates speciosus: identification of pumiliotoxin-A and allopumiliotoxin class alkaloids, 3,5-disubstituted indolizidines, 5-substituted 8-methylindolizidines, and a 2-methyl-6-nonyl-4-hydroxypiperidine. Journal of Natural Products. 1988 Nov-Dec;51(6):1188-97. PMID 3236011
- Daly JW, Garraffo HM, Spande TF, Clark VC, Ma J, Ziffer H, Cover JF Jr. Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates. Proceedings of the National Academy of Sciences USA. 2003 Sep 16;100(19):11092-7. PMID 12960405
- Comins DL, Huang S, McArdle CL, Ingalls CL. Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: a concise asymmetric synthesis of (+)-allopumiliotoxin 267A. Organic Letters. 2001 Feb 8;3(3):469-71. PMID 11428041
- Franklin AS, Overman LE. Total Syntheses of Pumiliotoxin A and Allopumiliotoxin Alkaloids. Interplay of Pharmacologically Active Natural Products and New Synthetic Methods and Strategies. Chemical Reviews 1996;96(1),505-522.
- Tang XQ, Montgomery J. Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B. Journal Of The American Chemical Society. 2000;122(29):6950-6954.
- Aoyagi S, Wang TC, Kibayashi C. Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel(II)/chromium(II)-mediated cyclization. Journal of the American Chemical Society 1993;115(24):11393-11409.